


Flappers and Philosophers

by bookishandbossy



Category: Gossip Girl (TV 2007)
Genre: 1920's AU, Banter, F/M, mostly a romantic comedy
Language: English
Status: Completed
Published: 2020-09-21
Updated: 2020-09-21
Packaged: 2021-03-07 17:54:27
Rating: General Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 4,435
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/26571775
Author URL: https://archiveofourown.org/users/bookishandbossy/pseuds/bookishandbossy
Summary: Dan Humphrey first meets Blair Waldorf at a party he's not invited to.  He doesn't mean to write a story that's all about her, but somehow it happens.  Blair Waldorf has every intention of giving an aspiring writer a sharp talking-to about the character he's based on her.  She doesn't mean to getfondof him, but somehow it happens.  (1920's AU)
Relationships: Dan Humphrey & Blair Waldorf, Dan Humphrey/Blair Waldorf
Comments: 15
Kudos: 100





	Flappers and Philosophers

**Author's Note:**

> Title is from the F. Scott Fitzgerald story collection.
> 
> This is part of my decades project, where I'm writing a different fic set in each decade of the twentieth century--come find me on Tumblr if you want to know more!

He first sees Blair Waldorf at a party he's not invited to. It's the kind of party people just turn up at, drinking someone else's champagne and eating someone else's food and getting horribly drunk and diving into someone else's pool. Dan hears about the party from Nate Archibald, who is actually invited because Nate is the kind of person who gets invited everywhere, and he goes because he's stuck on page three of his novel and he could use some inspiration. So he wanders through room after room of someone's mansion, taking notes on the massive swimming pool and gilded columns and library of unread books, and tries to come up with a metaphor that doesn't feel completely tired.

She's draped across a chaise longue wearing an impossible construction of silver beads and lace, looking beautiful and bored. She opens her eyes when he comes within six feet of her, flicks her gaze up and down him, and then shuts her eyes again.

“You really need to fire your tailor,” she says. “That suit is terrible.”

Dan doesn't even _have_ a tailor. 

“It's my only one,” he says. “I've never had any complaints about it.”

“If you only have one suit, what on earth are you doing at this party?” She says it like she honestly, truly can't comprehend what someone with one suit would be doing at the party, so sweet and innocent that it goes right back round to sharp again, and Dan feels himself bristle.

“I'm a writer. I came here for inspiration,” he says, feeling inside his jacket pocket for his little notebook as if she's about to demand proof. 

She arches one eyebrow at him. “Have I read anything you've written?”

“Probably not,” he admits. “At least not yet.”

“So you think I'm going to, then.” She has a paperback balanced on her lap and if Dan squints, he can just about make out the title. The Age of Innocence, by Wharton, and all of a sudden he feels the ridiculous impulse to ask her what she thought of it. 

“I think everyone's going to,” he blurts out and feels himself flush bright red. It's the kind of thing he says to himself late at night, when the words are flying out faster than he can write and even the tiny corner of New York he can see from his window seems to brim with possibility. Not the kind of thing he's ever dared to say out loud before. 

“Ambitious,” she says and goes back to her book. He's been dismissed. 

He finds out more about her from Nate afterward—Blair Waldorf of the New York Waldorfs, queen of the flapper set, favorite of the gossip columns, and, as of three months ago, no longer the fiancee of Chuck Bass, for reasons no one knows and everyone likes to speculate on—and he's...fascinated, in spite of himself. And he writes a story where the main character is maybe (definitely) based on her. And he sells it, for a tidy sum that buys him dinner for a week and a new hoard of paperbacks to clutter up his tiny room. And that, arguably, is where the trouble really starts. 

The story is terrible. It's a blatant imitation of Fitzgerald, overwritten and underbaked and featuring a main character who is decidedly not her but also somehow is. Blair seethes quietly about it and then less quietly, until Serena suggests she write a letter to the editor of the magazine that published it. 

She doesn't write a letter—instead, she terrorizes the editor into giving her Dan Humphrey's address and braves the train to Brooklyn to tell him exactly what she thinks of his story. 

“I have never filled a swimming pool with champagne,” she tells him when he finally swings open his door, shirt and hair hopelessly rumpled. Blair can't tell whether it's because he just woke up or because disheveled is simply Dan Humphrey's natural state of being. “First of all, it'd be a waste of good alcohol. Second of all, it'd get up your nose. Third--”

“What I wrote was fiction,” he says defensively and runs a hand through his hair, attempting to smooth it down. (It only makes the situation worse.)

She scoffs. “It's obviously me. Completely inaccurate but still me.”

He gapes at her. “That doesn't even make sense.”

Blair just crosses her arms and taps one T-strap heel against the stairs, waiting for him to give in. It takes him three minutes and twenty-seven seconds to cave. Better than she would have expected.

“Look, I'll admit that I wrote the first draft of that story the night of that party. I'd been stuck on what I was writing for days and so I thought I would go to see if I could find some inspiration there. Which I did. But it had nothing to do with you being rude to me in a library.”

There's nothing for it. Blair sighs and pulls the copy of his story that she's covered in notes in neat red ink out of her handbag. “I've identified five paragraphs in which it becomes clear that you've based this supposedly fictional socialite on me. Two focus on physical detail, one on my recent unfortunate engagement, one on my friendship with a blonde who you've very unimaginatively named Selina, one--”

“It wasn't on purpose,” he says and he's rude even in defeat. “I may have...drawn on a few things I knew about you while I was writing.”

“It's terrible manners to draw on people you don't know. Especially on unfounded rumor.”

“Correct the record, then.” He shrugs. “Take out a full-page advertisement in the Times—that ought to set the record straight.”

“So you can write another unflattering story about me?”

“It wasn't unflattering,” he protests. “You come off quite well in it.”

“I'm invited to a party this weekend,” she says before she can give in to the urge to tell him exactly how inaccurate the tragic flapper he's made her to be is. “It's bound to be extravagant and utterly tasteless. I'll take you with me, you can soak up all the atmosphere you like, and in exchange, there will be no more characters who bear even the slightest resemblance to me. Deal?”

“Three parties,” he counters. “And you can't just abandon me in a corner the entire night. I want introductions and the inside story on them.”

“Fair. Although, you can't do it in that suit. Or with that hair.” Blair narrows her eyes at him, appraising. She's not a miracle worker but she might be able to do something with the help of her mother's favorite tailor and the judicious use of scissors. “If you're going to be seen with me, you'll have to be held to a higher standard.”

Dan gets his measurements taken by a tiny old man who exclaims over the state of his clothes and trades despairing glances with Blair and gets his hair cut by a frankly terrifying woman with a nearly indecipherable French accent who carefully listens to Blair's instructions and then ignores everything he says. In between, she talks at him about fish forks and dance steps and commands him not to embarrass her anymore than he already has. He tries his best to grumble through it but there's a little part of him that's enjoying the way she rolls her eyes at anyone who gets in her way and moves the collar of his suit one inch to the left and then one inch to the right ad infinitum until she pronounces herself satisfied. Blair's not at all what he wrote her as, he's coming to realize, the beautiful broken sylph both at the heart of the party and hiding away from it. She's much more complicated—sharp and clever and prone to hyperbole and with the best eye for fabric and metaphors he's ever seen and yes, beautiful. (He's not blind, after all.)

She takes him to a party that's positively dripping with decadence and introduces him to everyone, hissing relevant details in his ear as she beckons them over. She downs three champagne cocktails in a row and still stays on her feet and when a few people deliberately turn their back as she comes near, she looks straight through them as if she doesn't exist. 

“My engagement didn't end well,” she tells him before he can ask. “My former fiance still isn't pleased about it.”

“Why did you leave?” He realizes that he's drunk far too much when he says it. Blair goes very still, one hand tightening around her champagne coupe, until she gives a little shake of her head and laughs, her earrings swaying with the motion.

“I'll only tell you if you promise not to put it in a story,” she says. “Now come on, I see Penelope over by the pool and she's practically guaranteed to say something ridiculous you can use.”

When he gets home that night at three in the morning, new suit miraculously preserved but hair absolutely hopeless, he types out six pages on his battered Smith Corona before stumbling into bed. He reads them in the morning and realizes at least a page and a half of it is about Blair. It isn't a direct version of her this time but rather bits and pieces. He's put her pearls around the neck of one character and her witticisms in the mouth of another and written her dark hair and silver dress into the background of every scene. He doesn't know how it happened.

But they had a deal and Dan Humphrey likes to think he's the kind of person who abides by the terms of a bargain. So he carefully edits any trace of her out and mails two versions to Blair's Upper East Side address, one with her in it and one without. Two days later, he receives a note from her on monogrammed stationery: _You might want to rethink that dialogue on the top of page eleven and you use the word avidly far too much. You can put that one comment I made about the ostrich feathers back in, though. It's too good not to be committed to print._

_You think I'm going to sell this story, then?_ he writes back.

_It's the least you could do after all the trouble I went to_ , she replies. 

He does sell the story and when Blair takes him to another party the next weekend, he sends her the story he writes afterward, too. 

Blair has a thousand better things to do with her time than be Dan Humphrey's editor. There are dresses to be fitted for and parties to attend and enemies to crush into tiny pieces. But none of them seem to be giving her quite the same satisfaction as taking out her fountain pen and covering his typewritten pages with notes until the original words are barely legible. Perhaps it's because while her mother contradicts her instructions to the dressmaker and everyone who attends the kind of parties she gets invited to persists in believing she still belongs to a man she left behind and even crushing one's enemies gets tiresome when one's done it as many times as she has, Dan Humphrey takes her notes. He argues with them about her, of course. They have a particularly spirited argument about his endings, which she maintains are uniformly dismal.

“Your stories don't all have to be so glum,” she complains, after he sends her one that ends with half the characters dying of the Spanish flu. “You let the reader think everything's going to turn out all right and then you introduce a sudden betrayal or a tragic train derailment to set everything wrong again. People don't like feeling unhappy when they're reading the Saturday Evening Post.”

“I don't believe in happy endings,” Dan says loftily. “Far too unrealistic.”

Blair makes a scoffing noise that Dan compares to a displeased cat and then they're arguing about animal metaphors and off on another thread entirely. The next thing that he sends her doesn't end happily, exactly. But there's a thread of hope in it that she's rather fond of. Because Dan Humphrey takes her notes and it's a surprisingly heady feeling. 

“Are you going to write a book?” she asks him. “You really ought to.” They're in a diner where there's no chance of them being seen by anyone she knows, with cups of dismal coffee and the pages of his latest effort spread out between them. (They've agreed that meeting in person is more efficient than posting pages back and forth between Brooklyn and New York.)

“I've been trying to write a book for the last three years,” he says and grimaces. “I can never get past page 30.”

“What you need is someone to hold you accountable,” she says. “Tragically, it would appear that this unfortunate task falls to me. I expect the first chapter by next Saturday.”

Dan groans and says that she's a merciless tyrant. He still sends her the first chapter by Saturday. It's not entirely terrible.

The three parties that she's promised to take him too come and go—Blair whispers particularly choice tidbits of gossip to him and Dan scrupulously keeps any explicit mention of her out of any more of his stories—and yet she keeps on taking him along with her. It's fashionable to be a patron of the arts, after all, and Dan's been doing much better with her assistance than he ever was before. One or two people at the parties even know who he is. Besides, Serena's off in California trying to be a movie star and it's nice to have someone else by her side. He keeps her arguing skills sharp and can occasionally be persuaded into bringing her drinks and makes her laugh in spite of herself. They read most of the same books so some nights, they just hide in the library of whatever mansion she's brought him to and pass novels back and forth, reading their favorite and least favorite passages aloud.

“Why were you in the library?” he asks, halfway through a chapter of Willa Cather “The night we met?”

“I was waiting to make my grand reappearance. You can't be too visible at these kinds of parties or people start to get bored with you,” she informs him. “Being young and beautiful and rich in New York City is all about knowing exactly how much of yourself to give the world and how much to keep for yourself.”

“I bet you practiced saying that in the mirror,” Dan says but his hand is fidgeting at his side and she knows he can't bear not being able to write it down right this instant. 

“Being young and beautiful and rich in New York is also about practice,” she says dryly. “And you can't use that one. I want to use it myself.”

“You write, then?” 

“Not fiction. It's essays mostly and so far it's only for myself. I'd like to edit a magazine, though,” she admits and feels a little whoosh of breath go out of her at the confession. She's told Serena, of course, but girls like Blair aren't supposed to aim for writing the society pages instead of being in them. And girls who are engaged to men like Chuck Bass aren't supposed to have ambitions of their own at all. 

“I think I'd be very good at telling people what to do,” she adds, trying to keep her voice light and even. “Look how well I've done with you.”

“People would beg for the privilege,” Dan says and his voice is light too but somehow she knows that he means it. 

The next night, after sitting through four interminable courses at someone's mansion and declining invitations to yet another grimy speakeasy, instead of going to bed at a reasonable hour to prevent the dark shadows from multiplying underneath her eyes, she finds herself reaching into the depths of her desk drawers and pulling out one of the pieces she's written. It needs some finessing, certainly, but it's not half bad. So Blair finds the glasses that she only wears in private and starts going over it with her engraved fountain pen. She submits it to a magazine under a pen name and when it's accepted, she's secretly, quietly delighted. It's delicious, the knowledge of seeing her name in print, and Blair hasn't had many delicious secrets in her life.

“This is you,” Dan says, pushing a copy of Vanity Fair across the table towards her. “Isn't it?”

And she wonders how he came to know her so well and why she doesn't mind it.

Serena wants Blair to go to Paris with her. (She very nearly was a movie star but then she had some kind of dramatic falling out with her director, who she was undoubtedly having an affair with, and now she wants to drown her woes in red wine and French couture, which Blair has to agree is an excellent plan.) Blair agrees, because she's always found it hard to say no to Serena, and books a first-class passage on the Cunard Line across the Atlantic. Dan will have to muddle along without her while she's gone. She'll leave instructions, of course, with lists of all the adjectives he tends to overuse, and he's become well known enough to occasionally be invited to parties of his own accord. 

She reminds him of all this when he blinks owlishly at her and says that he'll miss her.

“Nonsense,” Blair says. “I'd like to think that you'd fall apart without me but I'm forced to admit that you need my editorial skills far less frequently than you once did.”

“It's not that. I'll just miss you.” Dan turns slightly pink. He looks almost surprised that he said it and Blair is equally surprised to find that maybe, she'll miss him too. 

“You could come to Paris for a visit,” she blurts out. “Serena and I should be there for at least a few months. Plenty of time for you to fulfill your lifelong ambition of romantically starving in a Parisian garret.”

“I never said I wanted to starve in the garret,” Dan points out. But then his face lights up a little, a smile unfolding from one corner of his mouth and spreading across his face. “But I've always wanted to see Paris. So thank you.”

“Of course you do—you're not a complete heathen,” Blair says crisply. There's a hint—the barest hint, really—of affection in her voice and Dan smiles a little bit wider.

“I'm glad to have finally garnered a modicum of your approval.”

Inside her chest, her heart (traitorous organ) gives a little thump.

It's while Blair's in Paris and he's in New York that Dan makes proper progress on his novel. He writes like he's in a fever, waking up early and staying up late, the words pouring out of them onto the pages of his notebook and the cheap paper he stuffs into his typewriter and the backs of paper menus at the clubs he gets invited out to now, where he ignores the orchestras and the drinks and the merry chaos all around him and writes like a man possessed. And when he finally stops and goes through what he's written, he's forced to admit it. The novel is Blair. He started out well enough leaving her out of it but now she's etched onto every page and Dan can't decide if he needs to press it into her hands or burn every last page of it. 

Eventually, he packs the pages into his suitcase and gets on the boat to Paris. He's likely doomed. He thinks he wouldn't mind doom at the hands of Blair Waldorf. 

Dan arrives in Paris about a month after she's been there, thumbed-through guidebook in one hand and his notebook in the other, and before they go back to determinedly sparring, she thinks that he's glad to see her. He's rented a tiny attic room on the Left Bank, complete with noisy student neighbors who drink late into the night and ancient landlady who quizzes Dan on his comings and goings, and he seems to enjoy every bit of it, although Blair can't imagine how. He insists on sitting in smoky cafes in an attempt to get a glimpse of Hemingway, which Blair refuses to accompany him along to, and walks along the length of the Seine, which she does agree to. Dan is thrilled at everything he sees, from the soaring arches of the Eiffel Tower to the newspapers on sale in the kiosks that dot the streets of the city, and it sends a little thrill through Blair too. He reads aloud passages from his guidebook whenever they encounter something of architectural significance and she tells him all the stories that don't appear in it. (He suspects that she's made up at least half of them. He _might_ be right.) There's something natural about it, walking through the city together, his steps matching hers and their conversations seemingly never ending, and in New York, she would be courting scandal by doing it but here...here no one cares about her last name or who she was once engaged to and Blair feels something fragile and new opening up inside of her. 

She sells a series of columns to Vogue, about being an American in Paris, and Dan picks her up and spins her around when she tells him, whooping with delight in a way that's entirely unlike him. It's late and they've split an entire bottle of champagne between them at dinner, both flushed with the alcohol and excitement as they walk through the cobblestone streets. And it's the champagne that leads her to wait a few seconds before she demands that he put her down, enjoying the feel of his arms around her more than she should. 

“He's very handsome,” Serena says speculatively when Dan's got his back to them, peering intently at a painting in a corner of the Louvre. “In a rumpled sort of way.” 

“You do realize that if you break his heart, he'll never be able to finish his novel,” Blair says. “You'd be robbing the world of greatness.” 

Serena shrugs and laughs, already dismissing the prospect of Dan in favor of one of the handsome Frenchmen who's been casting hopeful glances at her from across the gallery, and they move on to talking about about the Schiaparelli gown Blair's been lusting after. But she can't forget the small hot flare of possessiveness that surged up in her chest when Serena mentioned the possibility of conducting an affair with Dan. _Mine_ , it says stubbornly, insistently, no matter how hard she tries to stifle it. 

“So are you finished with the book yet?” she asks him over coffee at Les Deux Magots. “I've been promising brilliance to everyone of significance I know and I'd hate to be proven wrong.” 

Dan looks about shiftily. “It's done. It's just—if I let you read it, you have to promise not to show up on my doorstep demanding revisions again.” 

“That was for your own good, Humphrey. But I promise to deliver all of my notes by mail so you can weep over them in private,” she says. 

Later that afternoon, a thick envelope stuffed full with typewritten pages arrives at Blair's suite in the Ritz. There's no note enclosed with it but she knows from the first paragraph that it's Dan. It's two in the morning when Blair finishes the pages and summons a taxi to take her from the comfort of the Ritz to Dan's alarmingly ramshackle building. It's later still when he swings open the door, shirt half-buttoned and askew, hair doing disgraceful things that shouldn't appeal to her at all. 

At first, he just blinks at her. “I suppose I deserve this,” he finally says after a minute or so of them staring at each other. “And if you'd like me to burn it and start over, I certainly can. I tried writing it without any of you in it but it didn't work any of the times that I tried it. I always got stuck on chapter three.” 

“It's not bad,” she admits. “Some parts of it are quite good. Complimentary, even. I didn't know you thought of me like that.” 

“I suppose I do. Didn't really realize it until I was writing it.” Dan tries to glance away and down at the floor but his eyes swing back up as if they're helplessly magnetized to her face and Blair feels heat rush to her cheeks and prays that the light is low enough that he can't see it. 

“You gave her a happy ending.” She shifts a little from foot to foot, suddenly conscious of the fact she's makeup-less and wearing last season's dress. “I thought you didn't believe in happy endings.” 

“I thought she deserved one. I—I wanted to give her that.” He looks at her a little helplessly and Blair knows. She knows that he doesn't know how to say it and neither does she and that for two writers, they can be rather hopeless with their words. So she surges forward into the doorway and kisses him. 

It's a force of a kiss and all the breath goes out of Dan when she first collides into him but then he slides an arm around her waist and pulls her up against him as he kisses her back, the other hand going into her hair and pulling all the pins out until it falls down around her shoulders. She's spent some (too much) time imagining what it might be like to kiss him but as it turns out, her fantasies were entirely too decorous. Dan kisses her like it's the only chance he'll get and it's intoxicating. 

“I feel bound to inform you that this very well could end in disaster,” she tells him when she finally pulls away to catch her breath. 

“I know,” he says. “I think I'll take that chance.” 

“You _are_ my favorite disaster,” she says and kisses him. Dan laughs and his arms go around her again and it's all sorts of sideways—her, in this tiny Parisian garret that's still lit by candlelight, kissing a boy from Brooklyn like she'll never stop, the things they both can only say without saying swirling around them—and somehow, Blair knows everything about it is right. 


End file.
